Florida Keys Annual Events

The Florida Keys has festivities taking place all through the year including concerts, festivals, fairs and sporting events. The list below presents an overview of the major events in the Florida Keys area.


Annual New Year’s Day Celebration

On Islamorada’s Founders Park, Mile Marker 87, a 5K run, walk and crawl kick off festivities at 8 a.m. for the new year, followed by a boat parade and more. Call (305) 853-1685 for more information.

Old Island Days House & Garden Tour #1

January brings Tour One of the annual visits to several historic homes and gardens. Call (305) 294-9501 for more information.

Annual Tennessee in Key West Seminar

A four-day celebration of Tennessee Williams’ works includes remembrances of Williams by friends and acquaintances. Call (888) 293-9291 for more information.


Old Island Days House & Garden Tour #2

February brings Tour Two of the annual visits to several historic homes and gardens. Call (305) 294-9501 for more information.

Old Island Days Arts Festival

Fine art takes center stage in Key West during this festival going strong for almost four decades. Call (305) 294-1241 for more information.

Pigeon Key Art Festival

Art festival takes place on the Old Seven Mile Bridge on Pigeon Key, once an encampment for workers of Henry Flagler’s Overseas Highway. Call (305) 743-7664 for more information.


Sombrero Beach Run

On the first Saturday in March, the Key West Southernmost Runners Club hosts a 10K Run and 5K Walk along Sombrero Beach in Marathon. Call (305) 289-9868 for more information.

Old Island Days House & Garden Tour #3

March brings Tour Three of the annual visits to several historic homes and gardens. Call (305) 294-9501 for more information.

Islamorada All-Tackle Bonefish Tournament

This all-release tournament features trophies and prizes. Call (305) 852-7706 for more information.

Marathon Seafood Festival

Great locally caught seafood cooked by anglers with live music at an annual extravaganza is staged by the Marathon Chamber of Commerce. Call (305) 743-5417 for more information.

Conch Shell Blowing Contest

As part of Old Island Days, contestants gather to produce novel sounds in a competition going strong for more than four decades. Call (305) 743-5417 for more information.


Art Festival Weekend

Over a weekend in mid-April, the Island Market Place in Key Largo hosts a festival of local arts, crafts, food and Keys culture. Call (305) 731-9558 for more information.

Annual Ladies Tarpon Tournament

This all-release tournament staged annually for some three decades is for women only. Call (305) 743-6139 for more information.

Conch Republic Independence Celebration

Parades, bed races, parties and all-around wackiness commemorate the unofficial April 23, 1982 founding of the Conch Republic. Call (305) 296-1213 for more information.

Robert Frost Poetry Festival

Poetry writing contest and workshop are staged at historic sites including the Robert Frost Cottage at Key West’s Heritage House Museum where the poet spent many winters. Call (305) 296-3573 for more information.


Taste of Islamorada

For more than a decade, the area’s best chefs have provided island dishes for all to enjoy. Call (305) 664-4503 for more information.

McDonald’s Tarpon Tournament

Tarpon, bonefish, redfish and snook are the hot commodities at this invitation tournament. Call (305) 743-6139 for more information.

Barley Bay Festival

Reef cleanup and concert benefit the Keys marine environment. Call (305) 451-4040 for more information.


Cuban American Heritage Festival

Cuban culture and customs are showcased in Key West during this mid-month festival. Call (305) 295-9665 for more information.

Dick Fuhr Memorial Fishing Tournament

Dolphin tournament with prizes benefits the Dick Fuhr Foundation. Call (305) 458-4257 for more information.

PrideFest Key West

Festival honors diversity, openness and freedom of a city consistently recognized as one of the world’s top gay and lesbian vacation destinations. Call (305) 292-3223 for more information.

Marathon Super Boat Grand Prix

High-speed power boats race in the heart of the Florida Keys. Call (305) 296-6166 for more information.


Annual Underwater Music Festival

Reef preservation is emphasized in the underwater radio broadcast for divers and snorkelers. Call (305) 872-2411 for more information.

Hemingway Days Festival

The legendary author’s work and lifestyle are highlighted, along with a look-alike contest. Call (305) 296-2388 for more information.


Key West Summer Food & Wine Festival

Late July and early August showcases talents of Key West master chefs and diversity of Florida Keys culinary offerings. Call (305) 296-6909 for more information.

Key Largo Offshore Classic

World-class high-speed powerboats compete in the second leg of the Florida Keys Offshore Triple Crown. Call (305) 923-9172 for more information.

Mercury Little Palm Island Grand Slam

On Little Torch Key, the all-release bonefish, tarpon and permit tournament has original and print artwork trophies. Call (305) 664-2002 for more information.


Key West Poker Run

Motorcycles cruise from Miami to Key West in mid-September to raise money for local charities. Call (305) 395-1198 for more information.

Marathon International Bonefish Tournament

Anglers gather for the all-release spin or fly event with trophies and evening social events. Call (305) 743-7368 for more information.


A lesbian-oriented festival of art shows, sailing and snorkeling, comedy performances and other activity. Call (305) 296-2491 for more information.


Fantasy Fest

In Key West, late October’s Fantasy Fest tops itself in wackiness every year. Call (305) 296-1817 for more information.

Florida Keys Birding & Wildlife Festival

Marathon and the Lower Keys host a celebration of Florida Keys wildlife at the peak of the fall birding season. Presentations and field trips focus on education. Call (305) 743-3900 for more information.

Fright Night at Holiday Isle

In Islamorada, Halloween fun at Holiday Isle includes a party, costumes and cash prizes. Call (305) 664-2321 for more information.


Parrot Heads in Paradise Convention

National and international clubs of Jimmy Buffett fans flock to the island that inspired the singer/songwriter/author’s hits like Margaritaville.

Pirates in Paradise Festival

Late November through early December brings the Pirates in Paradise Festival reprising the Golden Age of Sail with stuntmen, historic reenactors and improvisational actors invading Key West. Call (305) 296-9694 for more information.

Annual Corvettes in Paradise

The Florida Keys Corvette Club hosts a display of classic and modern cars. Call (305) 872-9641 for more information.


Annual Island Art Fair

On Big Pine Key, this nearly two-decade old event features artists, crafters and vendors displaying and selling. Call (305) 872-2411 for more information.

Lower Keys Christmas Boat Parade

All boats are welcome to participate in this favorite Lower Keys holiday event sponsored by the Lower Keys Rotary Club. Santa and Mrs. Claus are expected to arrive and hand out candy to the kids. Best viewing spots to watch the Pine Channel Causeway parade is from Kiki’s Sandbar, located at 183 Barry Ave., on Little Torch Key. Contact: Steve at 305-923-5370.

Key Largo Christmas Boat Parade

Decorated boats parade along the shoreline of Blackwater Sound. Call (305) 451-1592 for more information.

Key West Holiday Parade

Early December parade through Old Town kicks off the holiday season. Call (305) 292-8135 for more information.

Source: https://www.eventguide.com/floridakeys/